Structure of aldose condensation products with 2-hydroxyand 2-sulfanylbenzohydrazides |
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| Authors: | V V Alekseev A Yu Ershov B V Chernitsa V A Doroshenko I V Lagoda S I Yakimovich I V Zerova V V Pakal’nis V V Shamanin |
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| Institution: | 1.Military Medical Academy,Ministry of Defense of the Russian Federation,St.-Petersburg,Russia;2.Institute of High-Molecular Compounds,Russian Academy of Sciences,St.-Petersburg,Russia;3.Research Test Center of Medical and Biological Protection, State Research Test Institute of Military Medicine,Ministry of Defense of the Russian Federation,St.-Petersburg,Russia;4.St. Petersburg State University,St. Petersburg,Russia |
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| Abstract: | The structure of the condensation products of 2-hydroxy- and 2-sulfanylbenzohydrazides with a series of aldoses (L-arabinose,
D-ribose, L-ramnose, D-galactose, D-glucose, D-mannose) was studied by 1H and 13C NMR spectroscopy. The condensation products of monosaccharides with 2-hydroxybenzohydrazide in DMSO-d
6 solution exist as equilibrium mixtures of linear hydrazone and cyclic pyranose and furanose forms, the cyclic tautomers being
represented by two stereoisomers (α- and β-anomers). The aldose condensation products with 2-sulfanylbenzohydrazide in the
crystalline state have cyclic 1,3,4-benzothiadiazepine structure, while in DMSO-d
6 solution they undergo complete or partial isomerization into cyclic pyranose tautomer. |
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